


First Time for Everything

by cherry619



Category: Supernatural RPF
Genre: First Time, M/M, Prostitution, shy!Jensen
Language: English
Status: Completed
Published: 2013-04-25
Updated: 2013-04-25
Packaged: 2017-12-09 11:59:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,346
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/773951
Author URL: https://archiveofourown.org/users/cherry619/pseuds/cherry619
Summary: <blockquote class="userstuff">
              <p>Jensen is a shy man who listens to his friend Mike's advice and picks up a prostitute to finally lose his virginity. Of course Jared is in a whole nother league and Jensen's shyness keeps getting the best of him.</p>
            </blockquote>





	First Time for Everything

Jensen’s was so nervous his palms were sweating like crazy.  
  
He drove slowly, with his hands at 10 and 2 just like his Momma showed him when he first got behind the wheel. He feels his foot shaking on the pedal but he miraculously doesn’t crash. That could be because he’s only going 5 miles per hour. The street he is driving on is dark and sinister. It’s not called whore alley for nothing after all. Gangs, drug dealers, thugs and prostitutes out the ass roamed this street due to the less likely chance of getting busted.  
  
Why would one Jensen Ackles be driving down such a dangerous road? Well Jensen would really like to blame it on his friend, Mike Rosenbaum. He’s a boisterous man who likes to speak his opinion and be seen in a crowd. The complete opposite of Jensen, who was shy, timid, and really non approachable but somehow with his good looks men seemed to think that his aloof attitude was fucking hot and he usually had 2-3 offers for a date a day. But Jensen knew it was really because he’s easy to manipulate.  
  
Driving down the road, Jensen peered out of the window and searched for the tall man with floppy hair and supposedly a nice ass as Mike put it. Did Jensen mention he hates Mike? Due to Jensen’s shy personality, he usually ended dates before they even began. Jensen, as Mike put it, was the king of excuses. He remembered he even made up an elaborate lie about his sister giving birth in Wisconsin and having to make it there stat. He thought that one was quite good, but all he got was a smack upside the head from Mike.  
  
Which has led him to his current predicament. On this street, looking for this supposedly hot ass man who Mike said was actually a good friend of his. Jensen may be easy to manipulate but he isn’t stupid. This man is obviously a prostitute, a whore, a dirty hooker. The kind his momma warned him about as she clutched her Bible tightly to her chest. For some reason though, Jensen couldn’t say no to it. With Mike pleading with him to give it a try and his very vivid descriptions of the dude, how could Jensen say no?  
  
“God, I’m so fucking screwed,.” Jensen whispered.  
  
He pulled down the dark alley and had to ignore the present panic that was trying to escape. Looking from left to right he slowed down and stopped when he spotted a tall man leaning against the side of a building smoking a cigarette. Jensen’s SUV came to a stop as he just sat there and stared as the man unfolded himself from the shadows and walked into the dim light from the street lamps.  
  
“Holy shit!” Jensen gasped in awe. He rubbed his eyes to see if he was dreaming. The man was tall. That was the first thing that struck Jensen as he watched him flick his cigarette to the ground and stomp it out. His gorgeously long legs were encased in skintight leather pants that would make his momma instantly blush. Jensen’s eyes drank in the sight of his muscular legs as they traveled up to rest of the man; including his the present bulge in the pants, which tells Jensen the man is packing.  
  
He averts his eyes for a second and blushes like a fool making his freckles stand out in brief contrast. He didn’t know why he got like this. Mike liked to say it’s because his dick must be broken, but damn it Jensen’s dick was fully functioning! It’s just….he’s lost for words at the reason why he’s so shy. He would like to think it’s because he was brought up like a good Christian where sex, drugs, and rock and roll never really appealed to him much. Of course that all changed when he realized he wasn’t as straight as he thought and men turned him on much more than any woman could. Of course ever admitting this to his family is another story.  
  
Shaking himself of the thoughts, he focused on the man again and watched as his eyes danced in the dim lighting. A sexy grin lit up his face and he started making his way over to the side of Jensen’s SUV. Jensen panicked for a moment and fumbled to get the doors unlocked and roll down the window. Jensen was mesmerized with the way the man's hips swung back and forth. He could already feel his dick hardening; filling with blood at just the thought of the man.  _God I have spent way too much time with my right hand_  Jensen thought.  
  
“Hey there,” the man purred. His Texas accent coming out and shining through.  
  
“Uh…I…” Jensen stammered and blushed again when the man’s grin widened even more.  
  
“First time?” the man offered sympathetically. Jensen nodded his head up and down frantically, figuring his mouth wouldn’t be much help.  
  
“Well it’s alright man. How’s about we go back to your place? Then we can maybe chat for a little while?” The man’s voice became lower with the last statement and Jensen felt himself harden even more. Realizing he’d been staring at the man without giving any answer he reached over the seat and opened the door. Hey it’s the polite thing to do.  
  
The man grinned and hopped in, shutting the door silently behind him. Jensen found himself staring at the man’s face. How his perfect cheekbones accentuated the man’s smile. How his hazel eyes lit up whenever he talked.  
  
“Hello?” The man laughed when Jensen stopped daydreaming and focused on the hand that was waving in front of his face.  
  
“Did you go off to la la land dude?” Jensen blushed and scratched at his head.  
  
“Sorry,” he whispered. “I just…”  
  
  
“Hey,” the man said softly, settling his hand on Jensen’s. “It’s ok to be nervous.” Jensen swallowed and curled his hand into the man’s big palm. “Ok.” he whispered.  
  
“Awesome! So what’s your name? Mine’s Jared, but of course you can call me anything you like.” Jared winked at the end of that statement which only made Jensen blush even more.  
  
“I’m Jensen,” Jensen whispered shakily. He figured that Jared most be internally dying inside at the prospect of doing anything with this blushing virgin yet Jared never showed he was annoyed or upset. In fact, the whole way there Jared chatted about anything he could think of, which actually calmed Jensen down enough that he managed to stop blushing at everything Jared did or said. For some reason Jared’s banter made Jensen feel at home. Like he was talking with any of his neighbors or he was bantering back and forth with his brother.  
  
“So this is a really nice car you got here…must have cost a fortune!” Jared exclaimed while petting the dash like it was a small puppy. Jensen couldn’t help but laugh. An embarrassing snort came out that made him almost wish he was panicking again. At least he’d be too self-conscious to not try and laugh. Looking over at Jared with his cheeks aflame, he could only watch in wonderment as Jared leaned closer. Swallowing, Jensen felt himself trembling when Jared’s breath ghosted across the shell of his ear.  
  
“That was really hot right there,” Jared whispered. Jensen really didn’t know how to respond, so he let his body do the talking for him. “We’re almost here.” Jensen finally answered.  
  
This wasn’t really his apartment but rather a hotel room he booked for the two of them. He watched with amazement as Jared’s eyes widened at the huge hotel. In a way it made him sad to see how excited Jared got over an average hotel. It made him want to ask what led Jared to this kind of life.  
  
“Wow Jensen, this is…this is awesome! You didn’t have to book a hotel so fancy man.” Jared laughed giddily as he stared up at how many floors the hotel had. Jensen scratched his head and tried not to blush.  
  
“Well I wanted to…I mean if that’s ok of course.”  _Wow real smooth Ackles. Way to reel him in._  
  
“Jensen this is more than ok!” Jared said exasperated. He grabbed onto Jensen’s hand without a thought and dragged him into the lobby. Without even trying to, Jensen blushed at the hand to hand contact. But instead of fumbling to get loose he found himself wrapping his hand around Jared’s. The man’s childlike innocence was endearing and heartbreaking all at the same time. Jensen tried not to look at all the faces in the lobby. He could just imagine what they were saying about him and Jared. Jensen pulled on Jared’s hand and blushed again when Jared focused all his attention on him.  
  
“Maybe we should…you know…go upstairs?” Jensen’s hand twitched at wanting to scratch his head again but he put it in his pocket to stop it.  
  
“Of course! Sorry I get carried away sometimes.” Jared laughed and squeezed Jensen’s hand tighter. “Lead the way Casanova!”  
  
Jensen blushed and dragged Jared along to his room in silence. Unlocking the door with his key card, he awkwardly walked into the room. “Well uh…this is my room. Make yourself at home…I guess.” Despite his best efforts Jensen scratched his head again.  
  
Jared walked around before finally settling his eyes on the king size bed. He stopped and stared for a moment before running his fingers over the duvet.  
  
“Jared?” Jensen questioned both concerned and amused at the same time.  
  
“Shhh,” Jared whispered as he closed his eyes, feeling the fabric between his fingers. Jensen started to sweat again. What if Jared thought the room was wrong? What if Jared could sense when diseases hid in the blankets?  
  
“Jensen, you are so sweet to get me a room with silk,” Jared finally said, his grin lighting up again and showcasing his dimples. Jensen stared dumbly at the man before he let out a nervous laugh.  
  
“How did you know the covers were silk?” Jared gave him an incredulous look that instantly shut Jensen up.  
  
“Uh prostitute here!” Jared laughed, pointing to himself. “I probably know every fabric known to man by now.” Jensen blushed and fumbled to make it to the couch to maybe settle down and talk some. _What? Jared was the one who offered first._  
  
Drumming his fingers on his thigh, he froze when he felt Jared kneeling down before him. Jared’s fingers got to work on his thigh muscles and began massaging them with deft fingers. “Ja-Jared?” Jensen stammered nervously, trying to desperately hide the hard on he was sporting.  
  
“Shhh,” Jared whispered. “You’re so tense; let me relax you.” So for 10 minutes Jensen let Jared give him a massage. He tried not to let embarrassing groans escape but Jared was just so damn good! It was too hard to try and stifle them.  
  
  
“God Jared! How’d you learn to do that stuff?” Jensen whispered in awe after Jared kneaded out the last of the knots in his muscles. Jared’s face took on a weird look before he answered. “A John of mine was a physical therapist and liked to give massages a lot.”  
  
“Oh…” Jensen mumbled suddenly nervous again. “But doesn’t mean I don’t have tricks of my own,” Jared said with a gleam in his eyes. Suddenly Jensen felt as if he couldn’t breathe. This was really happening. He really was about to have sex, with a hooker no less. But hooker was such a harsh word. For some reason hooker and Jared just couldn’t be said in the same sentence.  
  
“Jared you know I…” Jensen blushed again and turned away in shame and embarrassment.  
  
“Hey,” Jared chided softly. “There’s a first time for everything man.” Jensen swallowed and looked into Jared’s earnest eyes. “We all have to start somewhere Jensen,” Jared said with a smile. Before Jensen knew it Jared was slowly unbuttoning his pants. Jensen swallowed a moan as Jared circled his hard dick inside his boxers. “I’m going to make it so good for you Jensen. Show you how awesome sex is,” Jared panted. Jensen couldn’t help but blush at the words, which only seemed to spur Jared on more.  
  
“Ok Jensen, I’m going to suck you off now, is that ok?” Jared asked slowly as his eyes hungrily devoured the man’s hardened cock in his boxers.  
  
“Oh shit!” Jensen moaned. “I….you’re going to give me a blow job?” Jensen asked with a blush. Jared laughed then smiled.  
  
“Yes, it’ll help relax you and I promise it’ll make you feel sooooo good.” Jensen didn’t doubt it would, but for some reason every time he thought of sex or anything relating to it he saw his momma…which was something he never wanted to associate together. Jared was already pulling out his cock though, whispering soft words that of course made Jensen blush. “God Jensen you feel so good. Such a big boy, aren’t you?” Jensen watched with fascination as Jared engulfed his hot member into his mouth. Suddenly lights danced across Jensen’s vision as every sense wheedled down to that one sensation.  
  
“Fuuuck!” Jensen cursed in pleasure as his hips suddenly started to work up into Jared’s mouth. But Jared held his hips down steadily and began to give Jensen his first ever blow job. Jared’s mouth was like a hot orifice that his dick craved. All the sensations, touches, hell even sounds, sent pleasure up his sensitive dick. Jensen’s eyeballs rolled in their sockets as he gripped the couch in a white knuckled lock.  
  
“Jared…God Jared!” Jensen screamed as he embarrassingly found himself already coming. Even with Jared’s steady grip, his hips moved some as his orgasm died down. Jared dutifully swallowed all of Jensen’s come until the last drop and licked the tip to collect more. Jensen head fell back with a boneless thud as he breathed heavily. His dick was still a little sensitive to the cool air around him.  
  
“God Jared that was…” Jensen didn’t even have a word for what it was. But Jared didn’t waste time on reliving the blow job. When Jensen peered up towards Jared, Jared was already stripping down. Jensen watched as Jared stripped the tight pants off his body. He swallowed and had to control himself so that he wouldn’t accidently come again. Jared’s cock, which was already hot and swollen popped out from the tight leather and stood to attention. Jensen’s eyes were blown wide with desire and lust. He had this feeling of just running over there and ravishing Jared, but his shy nature prevented him from living out his fantasy. Jared smiled and dug around in the pocket of his pants for lube and a condom. Jensen watched with curiosity as Jared made his way over to Jensen.  
  
“I’m sure you know what these are, right Jensen?” Jensen nodded his head up and down. “Good.” Jared smiled and sat directly on Jensen’s lap. Jensen moaned and bucked at the feeling of Jared’s ass brushing over his semi erect cock.  
  
“Shhh,” Jared whispered. Jensen nodded. Jared leaned in and kissed Jensen on the mouth. It was hot and quick as Jared’s tongue plundered into his mouth and felt around for Jensen’s own tongue. Jensen moaned and grabbed onto Jared’s hair.  
  
“Fuck Jared I…fuck!” Jensen cursed at his inability to portray what he wanted. To say what he felt and what he wanted to do. “I know baby. I know,” Jared said sympathetically. “I’ll get you there,” he whispered. Jensen nodded his thanks and relished in the way Jared sucked on his neck, then moved down to his shoulder until Jared finally had enough of Jensen’s shirt and tugged it off.  
  
Jensen grabbed onto Jared’s muscular back and closed his eyes. This was really it. He was about to have sex.  
  
“Now, Jensen, I’m going to ride you and show you how to pleasure someone, ok?” Jensen nodded, completely trusting Jared. “Ok.”  
  
“First we have to lube you up; then we have to prep me, ok?” Jensen nodded and watched as Jared popped the cap on lube and poured a liberal amount on his hand. He then slicked up Jensen’s cock making sure no area was untouched. Jensen gasped and moaned as Jared’s strong hand pulled and twisted his cock. Jerking him off as he was preparing him all at the same time.  
  
“Now we prep me,” Jared said with a wicked gleam in his eyes. Jared handed over the lube to him and Jensen held it with amazement and trepidation. What if he hurt Jared?  
  
  
“Slick up your fingers first.” Jensen did as he was told and held up his slick fingers. Jared leaned forward a little so his ass was in the air and Jensen’s hand could easily maneuver under him.  
  
“Now insert one finger and pull and push it out a little.” Jensen bit his lip and nervously maneuvered his finger to Jared’s ass. His hand was shaking but he felt around until he felt for Jared’s hole. Jared gasped and Jensen hurriedly pushed it in before he chickened out. He waited to see if Jared was hurting but the look on Jared’s face was one of pure pleasure as he desperately tried to get Jensen to move. Jensen repeated this step until he had Jared stretched open and ready for something bigger…Jensen’s cock.  
  
“Ok Jensen…God you’re doing so good baby! Now it’s the last step and the best,” Jared said as he lifted himself. “I want you to line your cock up with my ass, ok?” Jensen nodded and did as he was told. He could feel the tip of his cock hitting Jared’s hole. He moaned in pleasure and screwed his eyes shut. He could already feel pre come leaking steadily from his dick and he didn’t want to come now.  
  
“Fuck….Jensen I want you to push up as I push down ok?”  
  
“Ok…” Jensen whispered. “Fuck ok, on 3?”  
  
“Yeah,” Jared panted. “1…2…3!” Jared screamed as he pushed down as Jensen pushed up. Jensen’s head spun as Jared’s hole tightened on his sensitive dick. He almost wanted to come there but he remembered that he wanted this to last. Last forever if he could. “Fuck Jared!” Jensen cursed. “Move Jensen!” Jared demanded.  
  
And Jensen started to move. He thrust his hips up and down as Jared rode his dick like a horse. His body bumping up and down as Jensen’s dick slid in and out.  
  
“Fuck Jared! Fucking mother fucker!” Jensen cursed stupidly as he thrust up again into Jared’s tight heat. It was everything he ever dreamed of and more so. Just the feeling of Jared’s hole and all that heat made Jensen crazy with lust and desire.  
  
“Jensen….” Jared moaned. “Jensen!” Suddenly Jensen garnered some courage and latched onto Jared’s hard dick. “Fuck yeah….touch me Jensen.” With that as encouragement he began to jerk Jared off with hard, quick strokes. Groaning Jensen thrust up one more time and completely lost it. He screamed Jared’s name as he hurriedly jerked Jared off at the same time. His hips thrust up a couple more times before his orgasm died down. Jared took a little longer but also came with a scream. Jensen milked his dick and stroked him through his orgasm as Jared collapsed on top of Jensen. They stayed there for a while with Jensen still in Jared. Neither one had the energy to move or even clean themselves off. Jared groaned and nuzzled Jensen’s neck.  
  
“Fuck Jensen! You were so good.” Despite himself, he blushed at the compliment and scratched his head with his come-encrusted hand.  
  
“Jared…I…well you know…” Jared shut him up with a kiss on the lips. “Yeah I know I’ll see you next week.” Jensen smiled and let the lull of Jared’s heartbeat through his chest calm him down and relax him to sleep.  
  
 _ **The End**_


End file.
